Abstract
Four new structurally related metabolites, one γ-lactone named gliomasolide F (1), one δ-lactone named gliomasolide G (2), and two medium-chain fatty acids named gliomacids A–B (3–4), each containing nine carbons in total, were identified from the sponge-associated fungus Gliomastix sp. ZSDS1-F7-2. The planar chemical structures of these novel C9 metabolites were elucidated by nuclear magnetic resonance (NMR) spectroscopic methods, in connection with the analysis of high-resolution mass spectrometry (HRMS) and infrared (IR) data. The absolute configuration of 1, was determined by comparisons of experimental circular dichroism (CD) and optical rotation (OR) value with corresponding ones computed by quantum chemistry. The relative configuration of 2 was determined by the Nuclear Overhauser effect spectroscopy (NOESY) spectrum, while its absolute configuration was tentatively determined in view of the biogenetic and biosynthetic relationships between 1 and 2. Compounds 3–4, originally as an inseparable mixture, were successfully isolated after chemical modifications. The stereo-chemistries of compounds 3–4 were assumed by comparison of 13C NMR with those of the similar moiety reported in literature, in addition to the biogenetic and biosynthetic relationships with 1. The plausible biosynthetic relationships among these four C9 metabolites were supposed. Biologically, compounds 1–4 showed no cytotoxic effect against HeLa cell line at concentrations up to 25 μg/mL, while 1 exhibited moderate antifouling activity against the settlement of Balanus amphitrite larvae with IC50 being 12.8 μg/mL and LC50 > 25 μg/mL. The co-occurrence of macrolides gliomasolides A—E and four C9 metabolites in the same fermentation culture made us assume that these C9 metabolites might be biosynthetic building blocks toward the construction of more complex macrolides such as gliomasolides A—E or other unidentified polyketides.
Highlights
Marine sponge-associated microorganisms, known as one of the most prolific resources for the discovery of chemical and biological diversified secondary metabolites, have been and continue to be among the research interests of chemists and biologists worldwide [1,2,3,4,5,6,7]
A myriad of structurally unique and pharmacologically interesting drug leads have been decades, a myriad of structurally unique and pharmacologically interesting drug leads have been identified from the microorganisms derived from varieties of marine sponges, involving diterpenes identified from the microorganisms from varieties of marinedrug sponges, a myriad of structurally unique andderived pharmacologically interesting leads involving have beenditerpenes identified inhibiting the growth of a panel of cancer cell lines from a fungus Trichoderma harzianum inhibiting the growth ofderived a panel of varieties cancer cell lines sponges, from a fungus
This paper reported the isolation, structural elucidation, This paper reported the isolation, structural elucidation, relationship, andthe biological biosynthetic relationship, and biological effects of fourbiosynthetic new C9 metabolites from fungus biosynthetic relationship, and biological effects of four new C9 metabolites from the fungus effects of four new C9 metabolites from the fungus Gliomastix sp
Summary
Marine sponge-associated microorganisms, known as one of the most prolific resources for the discovery of chemical and biological diversified secondary metabolites, have been and continue to be among the research interests of chemists and biologists worldwide [1,2,3,4,5,6,7]. During the 2 past be among the research interests of chemists and biologists worldwide [1,2,3,4,5,6,7]. As part part of our continuous effort to identify structurally and biologically interesting natural natural products from marine resources [12,13,14], the fungus Gliomastix sp. A E with cytotoxic investigated with the discovery of a series effect against the growth of HeLa cell line [15].
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